Novel and highly efficient transformation of carbon dioxide into 2-oxazolidinones over Al-MCM-41 mesoporous-supported ionic liquids

References

• Fukuoka S, Fukawa I, Adachi T, et al. Industrialization and expansion of green sustainable chemical process: a review of non-phosgene polycarbonate from CO2. Org Process Res Dev. 2019;23:145–169.
   Web of Science ®Google Scholar
• Lee XY, Chew TL, Oh PC, et al. CO2 adsorption of MSU-2 synthesized by using nonionic polyethyleneoxide (PEO)-based surfactants. Chem Eng Commun. 2021;208:474–482.
   Web of Science ®Google Scholar
• Zhang S, Zhou Q, Jiang X, et al. Preparation and evaluation of nitrogen-tailored hierarchical meso-/micro-porous activated carbon for CO2 adsorption. Environ Technol. 2020;41:3544–3553.
   PubMed Web of Science ®Google Scholar
• Daglioglu ST, Karabey B, Ozdemir G, et al. CO2 utilization via a novel anaerobic bioprocess configuration with simulated gas mixture and real stack gas samples. Environ Technol. 2019;40:742–748.
   PubMed Web of Science ®Google Scholar
• Karapinar D, Creissen CE, de la Cruz JGR, et al. Electrochemical CO2 reduction to ethanol with copper-based catalysts. ACS Energy Lett. 2021;6:694–706.
   Web of Science ®Google Scholar
• Neves FF, Hoinaski L, Rörig LR, et al. Carbon biofixation and lipid composition of an acidophilic microalga cultivated on treated wastewater supplied with different CO2 levels. Environ Technol. 2019;40:3308–3317.
   PubMed Web of Science ®Google Scholar
• Rana AG, Ahmad W, Al-Matar A, et al. Synthesis and characterization of Cu-Zn/TiO2 for the photocatalytic conversion of CO2 to methane. Environ Technol. 2017;38:1085–1092.
   PubMed Web of Science ®Google Scholar
• Cai SF, Li HR, He LN. Bifunctionalization of unsaturated bonds via carboxylative cyclization with CO2: a sustainable access to heterocyclic compounds. Green Chem. 2021;23:9334–9347.
   Web of Science ®Google Scholar
• Li JH, Jia LQ, Jiang HF. Transition metal- catalyzed reactions in supercritical carbon dioxide. Chin J Org Chem. 2000;20:293–298.
   Web of Science ®Google Scholar
• Li X, Lang X, Song Q, et al. Cu(I)-catalyzed three-component reaction of propargylic alcohol,: secondary amines and atmospheric CO2. Chin J Org Chem. 2016;36:744–751.
   Web of Science ®Google Scholar
• Rostami A, Ebrahimi A, Sakhaee N, et al. Microwave-assisted electrostatically enhanced phenol-catalyzed synthesis of oxazolidinones. J Org Chem. 2022;87:40–55.
   PubMed Web of Science ®Google Scholar
• Hosseinian A, Ahmadi S, Mohammadi R, et al. Three-component reaction of amines,: epoxides, and carbon dioxide: a straightforward route to organic carbamates. J CO₂ Util. 2018;27:381–389.
   Web of Science ®Google Scholar
• Brunel P, Monot J, Kefalidis CE, et al. Valorization of CO2: preparation of 2-oxazolidinones by metal–ligand cooperative catalysis with SCS indenediide Pd complexes. ACS Catal. 2017;7:2652–2660.
   Web of Science ®Google Scholar
• Watile RA, Bagal DB, Patil YP, et al. Regioselective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines using Br−Ph3+P-PEG600-P+Ph3Br− as an efficient, homogenous recyclable catalyst at ambient conditions. Tetrahedron Lett. 2011;52:6383–6387.
   Web of Science ®Google Scholar
• Helal A, Fettouhi M, Arafat ME, et al. Nickel based metal-organic framework as catalyst for chemical fixation of CO2 in oxazolidinone synthesis. J CO₂ Util. 2021;50:101603.
   Web of Science ®Google Scholar
• Das R, Parihar V, Nagaraja CM. Strategic design of a bifunctional Ag(i)-grafted NHC-MOF for efficient chemical fixation of CO2 from a dilute gas under ambient conditions. Inorg Chem Front. 2022;9:2583–2593.
   Web of Science ®Google Scholar
• Kim JH, Lee SH, Kim NH, et al. Sustainable synthesis of five-membered heterocycles using carbon dioxide and Fe-iminopyridine catalysts. J CO₂ Util. 2021;50:101595.
   Web of Science ®Google Scholar
• Inagaki F, Maeda K, Nakazawa K, et al. Construction of the oxazolidinone framework from propargylamine and CO2 in air at ambient temperature: catalytic effect of a gold complex featuring an L2/Z-type ligand. Eur J Org Chem. 2018;23:2972–2976.
   Google Scholar
• Khatun R, Biswas S, Biswas IH, et al. Cu-NPs@COF: a potential heterogeneous catalyst for CO2 fixation to produce 2-oxazolidinones as well as benzimidazoles under moderate reaction conditions. J CO₂ Util. 2020;40:101180.
   Web of Science ®Google Scholar
• Xie YF, Guo C, Shi L, et al. Bifunctional organocatalysts for the conversion of CO2,: epoxides and aryl amines to 3-aryl-2-oxazolidinones. Org Biomol Chem. 2019;17:3497–3506.
   PubMed Web of Science ®Google Scholar
• Liu H, Hua R. Conversion of carbon dioxide into 2-oxazolidinones and 2(3H)-oxazolones catalyzed by 2,2′,2″-terpyridine. Tetrahedron. 2016;72:1200–1204.
   Web of Science ®Google Scholar
• Fiorani G, Guo W, Kleij AW. Sustainable conversion of carbon dioxide: the advent of organocatalysis. Green Chem. 2015;17:1375–1389.
   Web of Science ®Google Scholar
• Yuan YC, Sater MAE, Mellah M, et al. Enantiopure isothiourea@carbon-based support: stacking interactions for recycling a lewis base in asymmetric catalysis. Org Chem Front. 2021;8:4693–4699.
   Web of Science ®Google Scholar
• Chen JM, Qi L, Zhang L, et al. Copper/DTBP-promoted oxyselenation of propargylic amines with diselenides and CO2: synthesis of selenyl 2-oxazolidinones. J Org Chem. 2020;85:10924–10933.
   PubMed Web of Science ®Google Scholar
• Fujii A, Matsuo H, Choi JC, et al. Efficient synthesis of 2-oxazolidinones and quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by tetrabutylammonium fluoride. Tetrahedron. 2018;74:2914–2920.
   Web of Science ®Google Scholar
• Chen F, Tao S, Deng QQ, et al. Binuclear tridentate hemilabile copper(I) catalysts for utilization of CO2 into oxazolidinones from propargylic amines. J Org Chem. 2020;85:15197–15212.
   PubMed Web of Science ®Google Scholar
• Goossens K, Lava K, Bielawski CW, et al. Ionic liquid crystals: versatile materials. Chem Rev. 2016;116:4643–4807.
   PubMed Web of Science ®Google Scholar
• Depuydt D, den Bossche AV, Dehaen W, et al. Halogen-free synthesis of symmetrical 1,3-dialkylimidazolium ionic liquids using non-enolisable starting materials. RSC Adv. 2016;6:8848–8859.
   Web of Science ®Google Scholar
• Paschoal VH, Faria LFO, Ribeiro MCC. Vibrational spectroscopy of ionic liquids. Chem Rev. 2017;117:7053–7112.
   PubMed Web of Science ®Google Scholar
• Sood A, Thakur A, Ahuja SM. Recent advancements in ionic liquid based carbon capture technologies. Chem Eng Commun. 2021. DOI:10.1080/00986445.2021.1990886
   Web of Science ®Google Scholar
• Chasib KF, Mohsen AJ, Jisha KJ, et al. Extraction of phenolic pollutants from industrial wastewater using a bulk ionic liquid membrane technique. Environ Technol. 2022;43:1038–1049.
   PubMed Web of Science ®Google Scholar
• Ullah H, Wilfred CD, Shaharun MS. Green synthesis of copper nanoparticle using ionic liquid-based extraction from Polygonum minus and their applications. Environ Technol. 2019;40:3705–3712.
   PubMed Web of Science ®Google Scholar
• Baylan N, Çehreli S. Experimental and modeling study for the removal of formic acid through bulk ionic liquid membrane using response surface methodology. Chem Eng Commun. 2020;207:1426–1439.
   Web of Science ®Google Scholar
• Wang T, Zheng D, Zhang Z, et al. Exploration of catalytic species for highly efficient preparation of quinazoline-2,4(1H,3H)-diones by succinimide-based ionic liquids under atmospheric pressure: combination of experimental and theoretical study. Fuel. 2022;319:123628.
   Web of Science ®Google Scholar
• Gao XT, Gan CC, Liu SY, et al. Utilization of CO2 as a C1 building block in a tandem asymmetric A3 coupling-carboxylative cyclization sequence to 2-oxazolidinones. ACS Catal. 2017;7:8588–8593.
   Web of Science ®Google Scholar
• Huang M, Luo Z, Zhu T, et al. A theoretical study of the substituent effect on reactions of amines, carbon dioxide and ethylene oxide catalyzed by binary ionic liquids. RSC Adv. 2017;7:51521–51527.
   Web of Science ®Google Scholar
• Luo Z, Wang B, Liu Y, et al. Reaction mechanisms of carbon dioxide, ethylene oxide and amines catalyzed by ionic liquids BmimBr and BmimOAc: a DFT study. Phys Chem Chem Phys. 2016;18:27951–27957.
   PubMed Web of Science ®Google Scholar
• Song QW, Zhou ZH, He LN. Efficient,: selective and sustainable catalysis of carbon dioxide. Green Chem. 2017;19:3707–3728.
   Web of Science ®Google Scholar
• Xie WH, Yao X, Li H, et al. Biomass-based N-rich porous carbon materials for CO2 capture and in-situ conversion. ChemSusChem. 2022;15:e202201004.
   PubMed Web of Science ®Google Scholar
• ZhangX LH, Zhao FG, Cui XY, et al. Green process for hydrogenation of methyl ricinoleate to methyl 12-hydroxystearate over diatomite supported Cu/Ni bimetallic catalyst. Green Chem Eng. 2021;2:187–196.
   Google Scholar
• Wang WJ, Zhang YK, Wu AG, et al. Cost-effective 2D ultrathin metal-organic layers with bis-metallic catalytic sites for visible light-driven photocatalytic CO2 reduction. Chem Eur J. 2022;28:e202201767.
   PubMedGoogle Scholar
• Liu Y, Hu Y, Zhou J, et al. Polystyrene-supported novel imidazolium ionic liquids: highly efficient catalyst for the fixation of carbon dioxide under atmospheric pressure. Fuel. 2021;305:121495.
   Web of Science ®Google Scholar
• Liu Y, Hu Y, Zhang J, et al. SBA-15 supported pyrazolium ionic liquid efficient fixation of carbon dioxide into cyclic carbonate under mild conditions: the synergistic contribution of SBA-15 and pyrazolium ionic liquid. Micropor Mesopor Mater. 2022;337:111873.
   Web of Science ®Google Scholar
• Martinez AS, Hauzenberger C, Sahoo AR, et al. Continuous conversion of carbon dioxide to propylene carbonate with supported ionic liquids. ACS Sustain Chem Eng. 2018;6:13131–13139.
   Web of Science ®Google Scholar
• Askalany A, Olkis C, Bramanti E, et al. Silica-supported ionic liquids for heat-powered sorption desalination. ACS Appl Mater Interf. 2019;11:36497–36505.
   PubMed Web of Science ®Google Scholar
• He Q, O’Brien JW, Kitselman KA, et al. Synthesis of cyclic carbonates from CO2 and epoxides using ionic liquids and related catalysts including choline chloride-metal halide mixtures. Catal Sci Technol. 2014;4:1513–1528.
   Web of Science ®Google Scholar
• Xin B, Hao J. Imidazolium-based ionic liquids grafted on solid surfaces. Chem Soc Rev. 2014;43:7171–7187.
   PubMed Web of Science ®Google Scholar
• Hu YL, Li JR, Chen C, et al. Novel and sustainable synthesis of tetrahydrobenzo [b] pyrans using magnetic zinc ferrites modified SBA-15 supported ionic liquids as efficient and reusable catalysts. Sustain Chem Pharm. 2022;29:100779.
   Web of Science ®Google Scholar
• Li JR, Chen C, Liu XB, et al. Novel and sustainable carboxylation of terminal alkynes and CO2 to alkynyl carboxylic acids using triazolium ionic liquid-modified PMO-supported transition metal acetylacetonate as effective cooperative catalysts. Environ Sci Pollut Res. 2022;29:83247–83261.
   PubMed Web of Science ®Google Scholar
• Jadav D, Pandey DK, Patil T, et al. Ordered silica matrices supported ionic liquids as highly efficient catalysts for fine chemical synthesis. J Porous Mater. 2022;29:2003–2017.
   Web of Science ®Google Scholar
• Alirezvani Z, Dekamin MG, Valiey E. New hydrogen-bond-enriched 1,3,5-tris(2-hydroxyethyl) isocyanurate covalently functionalized MCM-41: an efficient and recoverable hybrid catalyst for convenient synthesis of acridinedione derivatives. ACS Omega. 2019;4:20618–20633.
   PubMed Web of Science ®Google Scholar
• Linares N, Silvestre-Albero AM, Serrano E, et al. Mesoporous materials for clean energy technologies. Chem Soc Rev. 2014;43:7681–7717.
   PubMed Web of Science ®Google Scholar
• Ye CP, Wang RN, Gao X, et al. CO2 capture performance of supported phosphonium dual amine-functionalized ionic liquids@MCM-41. Energy Fuel. 2020;34:14379–14387.
   Web of Science ®Google Scholar
• Trewyn BG, Whitman CM, Lin VSY. Morphological control of room-temperature ionic liquid templated mesoporous silica nanoparticles for controlled release of antibacterial agents. Nano Lett. 2004;4:2139–2143.
   Web of Science ®Google Scholar
• Bobadilla LF, Blasco T, Odriozola JA. Gold(III) stabilized over ionic liquids grafted on MCM-41 for highly efficient three-component coupling reactions. Phys Chem Chem Phys. 2013;15:16927–16934.
   PubMed Web of Science ®Google Scholar
• Zou B, Hu Y, Jiang L, et al. Mesoporous material SBA-15 modified by amino acid ionic liquid to immobilize lipase via ionic bonding and cross-linking method. Ind Eng Chem Res. 2013;52:2844–2851.
   Web of Science ®Google Scholar
• Tripathi AK, Verma YL, Singh RK. Thermal, electrical and structural studies on ionic liquid confined in ordered mesoporous MCM-41. J Mater Chem A. 2015;3:23809–23820.
   Web of Science ®Google Scholar
• Cheng T, Zhao Q, Zhang D, et al. Transition-metal-functionalized ordered mesoporous silicas: an overview of sustainable chiral catalysts for enantioselective transformations. Green Chem. 2015;17:2100–2122.
   Web of Science ®Google Scholar
• Liang Y. Recent advanced development of metal-loaded mesoporous organosilicas as catalytic nanoreactors. Nanoscale Adv. 2021;3:6827–6868.
   PubMed Web of Science ®Google Scholar
• Huo C, Ouyang J, Yang H. Cuo nanoparticles encapsulated inside Al-MCM-41 mesoporous materials via direct synthetic route. Sci Rep. 2014;4:3682.
   PubMed Web of Science ®Google Scholar
• Dardir FM, Ahmed EA, Soliman MF, et al. Synthesis of chitosan/Al-MCM-41 nanocomposite from natural microcline as a carrier for levofloxacin drug of controlled loading and release properties; Equilibrium, release kinetic, and cytotoxicity. Colloid Surface A. 2021;624:126805.
   Google Scholar
• Boldrini DE, Angeletti S, Cervellini PM, et al. Highly ordered mesoporous Al-MCM-41 synthesis through valorization of natural sediment. ACS Sustain Chem Eng. 2019;7:4684–4691.
   Web of Science ®Google Scholar
• Zhang L, Gao X, Zhang Z, et al. A doping lattice of aluminum and copper with accelerated electron transfer process and enhanced reductive degradation performance. Sci Rep. 2016;6:31797.
   PubMed Web of Science ®Google Scholar
• Imyen T, Yigit N, Dittanet P, et al. Characterization of Cu-Zn/core-shell Al-MCM-41 as a catalyst for reduction of NO: effect of Zn promoter. Ind Eng Chem Res. 2016;55:13050–13061.
   Web of Science ®Google Scholar
• Yoshitake H, Otsuka R. Grafting of precoordinated Cu2+–N-(2-aminoethyl)aminopropylsilane complexes onto mesoporous silicas and the adsorption of aqueous selenate on them. Langmuir. 2013;29:10513–10520.
   PubMed Web of Science ®Google Scholar
• Chenakin SP, Melaet G, Szukiewicz R, et al. XPS study of the surface chemical state of a Pd/(SiO2 + TiO2) catalyst after methane oxidation and SO2 treatment. J Catal. 2014;312:1–11.
   Web of Science ®Google Scholar
• Näslund LÅ, Persson I. XPS spectra curve fittings of Ti3C2Tx based on first principles thinking. Appl Surf Sci. 2022;593:153442.
   Web of Science ®Google Scholar
• Wang S, Lou F, Yu C, et al. Influence of Al3+ and P5+ ion contents on the valence state of Yb3+ ions and the dispersion effect of Al3+ and P5+ ions on Yb3+ ions in silica glass. J Mater Chem C. 2014;2:4406–4414.
   Web of Science ®Google Scholar